I often get some form of the question: "How did you transition from being a lawyer to an illustrator? When did you know when to transition? What did you do before you made the move?" I've done a few interviews on this topic now (see Press section on About page), and my latest collaboration with Skillshare Audio also addresses it (available here). But I want to consolidate it even more.
Here is a compilation of the advice I have given over the years:
1. Start With Why
Be clear on why you are thinking of a career change. If you're just running away from problems, avoiding hard work, or hoping it will give you validation from others, that's going to be a weak foot to start on. But if you're motivated from a true place of genuine passion and/or service, that's going to carry you through the challenges you'll inevitably face. 
Carefully consider your unique strengths and weaknesses. Go ahead and take those Strengths Finder tests if you'd like. Spend time reflecting. Go and explore different activities. Watch documentaries on different careers. Be curious about life and people and be inquisitive. Then reflect on your observations and experiences. Even when you're at the job you want to leave—start to look at it with a curious eye. What do you naturally enjoy doing? What do you hate doing? Why do you enjoy or hate these tasks? What is truly important to you in life? And write these things down. I have always kept a journal and I journaled a lot while considered my career change. I even had a chart with two columns of "things I want" and "things I don't want." It changes of course, but it's a good guide. Eventually, your "why" will start to crystallize. It doesn't have exact. It can be general direction.
For me, when I left law I didn't even know you could be a freelance illustrator. I just knew I had to move towards a more creative career that was meaningful. Upon my reflections, what spoke to me most is that the inner voice desiring creative expression—the same voice I had inside as a child that people told me I would eventually grow out of—was only getting louder and louder. My "why" was not that I hated law and wanted to escape at any cost. My "why" was that I wanted to do something that made me feel alive, and I had an inkling of what direction to head in. And from there, I continued this cycle of experience & reflection, picking up clues along the way. I actively return to and clarify my "why" all the time.
More recently, I have developed a daily meditation habit which has helped even more. I think it's a wonderful practice, and it's free. All you need is to carve out time for it. Right now we are blessed with time. Some people fear spending alone time with their thoughts, but then how will you ever get to know who you really are? We should learn to become good at being alone in self-reflection, to be able to process our thoughts in a loving way without judging ourselves. It is in the healthy balance of interaction with others and introspection with ourselves that we will find our answers.
2. You Are Creative—Keep An Open Mind!
Too many people think being creative is only for the artistic. All humans are creative. We are born to create. Your creative talents may be in something not obviously creative: you are excellent at organizing, you are excellent at sales, you are excellent at cooking, you are excellent at teaching. Don't limit yourself to what seems like traditionally sexy creative fields. Figure out what you love, without any dogmatic concepts, and explore how others are doing it to make a living. And don't get discouraged that you aren't good at it right away—that's completely normal. It takes practice, just like anything else!
3. Make A Plan. Save Your Money.
Ok let's talk about the actual transitioning. Most people's first concern is finances, and I was no exception. I am not independently wealthy, I was not going to receive money from family, and I didn't have a partner who could support me financially. So then what?
I spent about two years planning my departure from law. I paid off my student loans, saved everything I could, and I put a down payment on my house before leaving. A lot of people get caught up in spending money as soon as they earn it. Then they get stuck because they get used to affording those things. In our field we called it "golden handcuffs." I avoided that trap of tying my happiness to a never-ending pursuit of material upgrades. I only marginally upgraded my life after I went from being a poor grad student to making six figures. I bought a couple nice things. I ate out more often. I was able to finally be generous with friends and make donations. But beyond that, I kept a tight budget, saved as much as I could, made financial goals, and hit them. 
Note: This can be hard when all your friends are spending lavishly on food and cars and jewelry, but here's my view on that: (1) keep your eye on the prize; a meaningful life is so much richer than any object your money could buy, and (2) think for yourself and don't deny yourself small pleasures. Do you REALLY want that expensive watch or did advertising and social pretentiousness make you think you do? If you've really thought about it and decided "yes, I am genuinely passionate about wine, it brings me true joy," then let that be your splurge and forget the rest. 
Here's something I think everyone should know: there are many happiness studies that find that people don't get that much happier after hitting a certain basic level of standard of living. That's about a $70-85K annual salary (depending on where you live and how much other debt you have). That might sound like a lot to some people, and very little to others. You realize everything is relative, but this threshold helps keep things in perspective and achievable. I can personally attest that doing something you love is worth so much money. Making $80K doing something you love feels so much better than making $250K doing something you hate. I promise.
Yes times are different now (I'm writing this during the COVID-19 pandemic), but as past doors close, different doors open. And yes not everyone makes six figures in their lifetimes. But there's a version of this for every situation. After law, I voluntarily took a six figure pay cut and made five figures at a design agency. From there I again voluntarily took another pay cut and made pretty much nothing when I started my freelance illustration career. That might sound totally crazy to most people, but I want to show that it's possible. 
I relied on my own savings to tide me over for six months. I should also mention that at the time, I was going through a traumatic breakup of my long-term relationship. So not only was I going through a major career transition, I was single with a mortgage. That was hard (to put it mildly), but it also forced me to be serious and work hard. The whole time, I was extremely careful with my budget. I adjusted my spending as my circumstances changed. As always, I kept my eyes on the prize: doing something I love.
I truly believe if you love something, you can get good at it, and if you can figure out how it helps others, you will make a living. There is actually great freedom to learn you don't need to live in fear relying on an employer or the government. 
So save as much of your current salary or unemployment money as possible. Figure out ways to downsize if possible; there's no shame in that. Don't believe luxuries such as eating out and buying new clothes every season is something you have to have in order to be happy. Don't buy into manufactured lifestyles of social media, which uses this new form of subliminal advertising to feed their own version of "golden handcuffs" or "comparison depression" into your brain. It's not that you don't deserve these things; I hope one day everyone will be able to enjoy such nice things. But feeling like you deserve them when you can't afford them makes you operate with frustrated negative energy, and doesn't help you. 
Find happiness in things that don't cost money, such as hiking, meditation and video chats with friends. Find your joy and purpose, and you will be guided to a more abundant life. 
4. It Is Scary, And That's OK
 I was raised to avoid things that are scary or risky. I pursued a predictable life of academic achievement, which is not a bad thing. But when you are pushed to confront change, learning how to face fear is just a critical a life skill as doing well at school. Change is inevitable. Scary doesn't equal bad. I don't even think you have to be "fearless," because who is truly without fear? Not me. We just need to be able to be brave to confront fear. That's part of our humanity and part of what will lead to our growth and better life. 
5. Keep Learning
I went to a UCLA's well-regarded law school to become a lawyer. I value and appreciate a formal education. But for so many jobs out there, especially the newer future-ready ones, an expensive formal education is not necessary. Predatory student debt can be debilitating to enjoying what you do. So avoid it when you can. There are so many learning resources online that are affordable or even free. You can teach yourself so many skills from experts who have made their knowledge widely available. Create your own syllabus. Make a learning schedule. Learn from people you admire. Yes it is hard! See #4. But don't give up. Of course it's hard and takes time; anything worth doing is hard work. But there's pride to be found in that, not defeat. Again it's all about mindset. 
6. Be Your Own Dream Client
One piece of advice I like to share is to create your own passion project to learn the skills you want. I am not very great at learning when I'm bored. When I was transitioning, I created my own passion projects which forced me to learn the skills I needed (drawing, Photoshop, etc.). I created calendars, books, and other designs that attracted the attention of clients. It's a self-feeding cycle. Of course, if your passion project is too niche it will naturally be more limited it how much attention it attracts. Life is about finding a middle way. 
7. Ebb and Flow
Everyone is in a different situation so it's hard to provide specific advice. You may be single, childless, with savings, and roof over your head. That's a great place to start because it means you have time! On the other hand, you may have a child, or are caring for elderly parents, or dealing with a toxic relationship. That's more challenging, but by no means impossible. There are lots of stories of people making wonderful transitions in all of these situations. One advice that I think applies to anyone is to ebb and flow. When you are in a position to work hard, do it. When you are needing a break, take care of yourself. Don't be rigid and obsessive. To often people become depressed and paralyzed because they focus too much on what they lack and too little on all the tools they already have. Turn your perceived weaknesses and unfortunate circumstances into your strength and lucky break. Have confidence in your vision and motivate yourself from a place of genuine positivity and abundance.
8. Be Kind... and Put Yourself Out There!
Lastly, be kind. Being a pleasure to work with leads to more clients. Being nice to strangers leads to unexpected connections. I don't like traditional networking (e.g. schmooze fests) and I don't do it. But I am nice to whoever I happen to meet in day to day life. I'm courteous to any client I work with, even if they turn out to be a bit challenging. Don't be afraid to put yourself out there. That's how I got started and how I kept going. Plus it just makes the everyday more enjoyable when you have that approach to life.
I want to leave you with one last quote by Ira Glass, below. I found this to be so true, and it helped me push through those tough first few years of learning a brand new skill while transitioning careers.

Wishing you all the best -M
"Nobody tells this to people who are beginners. I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it's just not that good. It's trying to be good. It has potential. But it's not. But your taste—the thing that got you into the game—is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. 
Most people I know who do interesting, creative work went through years of this. We know our work doesn't have this special thing that we want it to have. We all go through this. And if you are just starting out, or you are still in this phase, you gotta know it's normal. And the most important think you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap. And your work will be as good as your ambitions." 
-Ira Glass

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